1. Round | 12/03/2023 | Tampa Bay Rowdies | - | Indy Eleven | 1:1 | ||||
2. Round | 02/04/2023 | Tampa Bay Rowdies | - | Birmingham Legion | 0:2 | ||||
2. Round | 09/04/2023 | Tampa Bay Rowdies | - | Miami FC | 2:0 | ||||
2. Round | 13/04/2023 | Tampa Bay Rowdies | - | Charleston Battery | 1:2 | ||||
7. Round | 03/09/2023 | Tampa Bay Rowdies | - | Hartford Athletic | 2:1 | ||||
7. Round | 07/09/2023 | Memphis 901 | - | Tampa Bay Rowdies | 3:2 | ||||
7. Round | 10/09/2023 | Tampa Bay Rowdies | - | Louisville City FC | 2:1 | ||||
7. Round | 17/09/2023 | San Antonio FC | - | Tampa Bay Rowdies | 3:3 | ||||
7. Round | 24/09/2023 | Tampa Bay Rowdies | - | Memphis 901 | 2:4 | ||||
7. Round | 28/09/2023 | Hartford Athletic | - | Tampa Bay Rowdies | 0:2 | ||||
7. Round | 01/10/2023 | Tampa Bay Rowdies | - | Loudoun United | 1:0 | ||||
8. Round | 08/10/2023 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 0:2 | ||||
8. Round | 15/10/2023 | Louisville City FC | - | Tampa Bay Rowdies | 2:3 |